Ammonium Chloride → (2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

n-BuLi (0.96 mL, 1.54 mmol, 1.6 M in hexanes) was added drop-wise to a solution of 1-hydroxymethyl-3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (600 mg, 1.54 mmol), prepared as in example la, in THF (30 mL) at 0° C. After 10 min bis(p-nitrophenyl)carbonate (600 mg, 1.96 mmol) was added. The solution was stirred at 0° C. for 20 min. A solution of 1-aminoethanol (128 mg, 2.10 mmol) was added. The resulting mixture was stirred at 0° C. for 30 min. Aqueous NH4Cl was added and the mixture was extracted with EtOAc. The organic extract was washed with brine and dried over MgSO4. Evaporation of the solvents and chromatography of the residue over silica gel using 1:1-3:2 EtOAc/hexanes gave (2-hydoxy-ethyl)-carbamic acid 3-(1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-pyrrol-1-ylmethyl ester (339 mg, 47%).

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